"On Water" Metal-Catalyst-Free Oxidative Coupling-Amidation of Amines To Access Imines and Amides

Author(s)

de Souza, Gabriela F. P. ; von Zuben, Theodora W. ; Salles, Airton G., Jr.

• Document type: Journal article
• Source: ACS SUSTAINABLE CHEMISTRY & ENGINEERING; v. 5, n. 9, p. 8-pg., 2017-09-01.

Abstract

A simple route toward the selective synthesis of imines and amides through oxidative couplingoxidative amidation of amines using widely available NaOCl is presented. Under this approach, unprecedented one-pot synthesis of symmetrical and unsymmetrical secondary amides from primary amines as a single starting material is reported. This metal-catalyst-free protocol relies upon on water acceleration to obtain the desired products in high yields. An additive-based robustness screen was conducted to demonstrate the high reaction tolerance to several chemical motifs. Furthermore, mechanistic studies support a proposed pathway for the targeted oxidation products. (AU)

• FAPESP's process: 15/12305-6 - Supramolecular Catalysis in water: Probing the influence of a tetrahedral cage on photocyclization and photooxidation.
• Grantee: Airton Goncalves Salles Junior
• Support Opportunities: Regular Research Grants